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raffish

Someone raffish is a bit of a scoundrel, carelessly making mischief. Your raffish classmate might constantly play mean practical jokes, always denying responsibility with a charming smile.

If you're raffish, you're a "rake" or a "cad." Though you're pretty much bad news, you pull off your dastardly deeds in an attractive manner. Someone with a raffish look is intriguing as well as disreputable. Raffish comes from riff-raff, "generally undesirable people," from the Medieval French rifle et rafle, "stealing from the bodies of the dead on the battlefield."

Definitions of raffish
  1. adjective
    marked by a carefree unconventionality or disreputableness
    “"a cocktail party given by some... raffish bachelors"- Crary Moore”
    synonyms: devil-may-care, rakish
    unconventional
    not conventional or conformist
  2. adjective
    marked by up-to-dateness in dress and manners
    synonyms: dapper, dashing, jaunty, natty, rakish, snappy, spiffy, spruce
    fashionable, stylish
    being or in accordance with current social fashions
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